Day Trips Across the Northeast

Escape the daily grind with an unforgettable one-day road trip in the Northeast. At Guess Where Trips, we curate unique, stress-free itineraries that let you explore the hidden gems in New England, New York, Pennsylvania and New Jersey. From scenic drives through rolling farmlands to charming small towns brimming with history, our surprise one-day road trips are designed to offer adventure and relaxation in equal measure.

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Featured Road Trips in the Northeast

  • BEST SELLING GIFT
    Tiny Town Tour

    Tiny Town Tour

    $65 CAD
    • Dog-Friendly
    Can depart from: Washington DC Area, Baltimore Area, Winchester VA Area, Alexandria VA Area
  • GREAT FOR A WEEKEND AWAY
    Winding Roads & Historic Gems

    Winding Roads & Historic Gems

    $65 CAD
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
    Can depart from: Washington DC Area, Baltimore Area, Winchester VA Area, Alexandria VA Area
  • Can be done in winter
    Haunts, Hikes & History

    Haunts, Hikes & History

    $65 CAD
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Washington DC Area, Baltimore Area, Alexandria VA Area, Winchester VA Area
  • BEST SELLING GIFT
    Whimsical Wonders

    Whimsical Wonders

    $65 CAD
    • Kid-Friendly
    • Accessible
    Can depart from: Philadelphia Area, Trenton Area, Baltimore Area
  • BEST SELLING GIFT
    Along the River

    Along the River

    $65 CAD
    • Accessible
    • Kid-Friendly
    Can depart from: Philadelphia Area, Trenton Area, Baltimore Area, Allentown, PA Area, Newark Area, Wilmington, DE Area, New York City Area
  • Best done Spring - Fall
    Waterside Bliss

    Waterside Bliss

    $65 CAD
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Washington DC Area, Baltimore Area, Alexandria VA Area
  • BEST SELLING GIFT
    Hudson River Hideaways

    Hudson River Hideaways

    $65 CAD
    • Dog-Friendly
    Can depart from: New York City Area, Newark Area, Hartford Area, New Haven Area
  • Can be done in winter
    Vibrant Vistas & Picturesque Towns

    Vibrant Vistas & Picturesque Towns

    $65 CAD
    • Dog-Friendly
    Can depart from: Hartford Area, New Haven Area, Springfield, MA Area
  • WINTER TRIP
    Black and white photo of an old house.

    An Unusual Adventure

    $65 CAD
    • Dog-Friendly
    Can depart from: Philadelphia Area, Trenton Area, Wilmington, DE Area
  • A PERFECT COUNTRYSIDE DRIVE
    Red covered bridge over water.

    Covered Bridges & Baked Goods

    $65 CAD
    • Kid-Friendly
    • Accessible
    Can depart from: Philadelphia Area, Trenton Area, Baltimore Area, Allentown, PA Area, Wilmington, DE Area
  • Can be done in winter
    Secrets of Gettysburg

    Secrets of Gettysburg

    $65 CAD
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Washington DC Area, Baltimore Area, Alexandria VA Area, Winchester VA Area
  • BEST DONE SPRING-FALL
    The Shore Explorer

    The Shore Explorer

    $65 CAD
    • Dog-Friendly
    • Accessible
    • Kid-Friendly
    Can depart from: New York City Area, Trenton Area, Newark Area, Philadelphia Area
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